2,3-Dihydroxyxanthone | 33018-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,3-Dihydroxyxanthone
• 英文别名: 2,3-dihydroxy-9H-xanthen-9-one；2,3-dihydroxy-xanthone；2,3-dihydroxy-xanthen-9-one；2,3-Dihydroxy-xanthen-9-on；2,3-Dihydroxy-xanthon；2,3-dihydroxyxanthen-9-one
• CAS: 33018-30-3
• 化学式: C₁₃H₈O₄
• 分子量: 228.204
• InChiKey: PCVZOSVNSMRPQO-UHFFFAOYSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 、 2,3-Dihydroxyxanthone 在 sodium acetate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 丙酮 为溶剂， 以4%的产率得到(+/-)-trans-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-11H-1,4-dioxino[2,3-b]xanthen-11-one
  参考文献：
  名称：

  摘要：

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

  DOI：

  10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 在 sodium hydroxide 、 三氯化铝 、 硫酸 、 铜 、 potassium carbonate 、 乙酰氯 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 甲苯 为溶剂， 反应 130.17h， 生成 2,3-Dihydroxyxanthone
  参考文献：
  名称：

  摘要：

  The synthesis, structure elucidation, and biological activities of five isomeric xanthonolignoids. (+/-)-trans-kielcorin C, (+/-)-cis-kielcorin C, (+/-)-trans-kielcorin D, (+/-)-trans-isokielcorin D. and (+/-)-trans-kielcorin E, are reported. The synthetic approach is based on the oxidative coupling of coniferyl alcohol with an appropriate xanthone. The influence of different oxidizing agents was studied, and the best results were obtained with potassium hexacyanoferrate(III). The structure elucidation was achieved by 2D-NMR techniques such as COSY, HETCOR, HSQC, and HMBC. Long-range C,H connectivities were used to establish the orientation of the substituents on the 1,4-dioxine rings, while NOE experiments were used to determine the confil-urations of these rings. These xanthonolignoids. as well as (+/-)-trans-kielcorin, (+/-)-trans-kielcorin B, (+/-)-trans-isokielcorin B. and the xanthonic building blocks 3,4-. 1,2-, and 2.3-dihydroxy-9H-xanthen-9-ones. and 2,3-dihydroxy-4-methoxy-9H-xanthen-9-one. were evaluated for their in vitro effect on the growth of three human cancer cell lines, MCF-7 (breast), TK-10 (renal), and UACC-62 (melanoma), and on the proliferation of human lymphocytes.

  DOI：

  10.1002/1522-2675(200209)85:9<2862::aid-hlca2862>3.0.co;2-r

文献信息

• γ-pyrone compounds. IV: Synthesis and antiplatelet effects of mono- and dioxygenated xanthones and xanthonoxypropanolamine
  作者：Chun-Nan Lin、Shorong-Shii Liou、Feng-Nien Ko、Che-Ming Teng

  DOI：10.1002/jps.2600820103

  日期：1993.1

  xanthodilol, 2,3-dihydroxyxanthone diacetate, and 3,4-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate- and collagen-induced aggregation. 3,5-Dihydroxyxanthone and its diacetate, 1,6-dimethoxyxanthone, and 3,6-dihydroxyxanthone and its diacetate showed potent antiplatelet effects on arachidonate-induced aggregation.

  由二苯甲酮前体合成黄原醇，单和双氧合的氧杂蒽，以及1,3-，2,3-，3,4-，3,5-，1,6-，2,6-和3,6-二氧合的氧杂蒽由Friedel-Crafts酰化，然后进行碱催化的环化反应以消除甲醇。3-羟-吨酮，黄酮醇，2,3-二羟x吨酮二乙酸盐和3,4-二羟di吨酮及其二乙酸盐对花生四烯酸和胶原诱导的聚集表现出有效的抗血小板作用。3,5-二羟基黄酮及其双乙酸盐，1,6-二甲氧基黄酮和3,6-二羟基黄酮及其二乙酸盐对花生四烯酸诱导的聚集表现出有效的抗血小板作用。
• Controlling Molecular Rotary Motion with a Self-Complexing Lock
  作者：Da-Hui Qu、Ben L. Feringa

  DOI：10.1002/anie.200906064

  日期：2010.2.1

  key to motion: A second‐generation molecular rotary motor, which contains a DB24C8 macrocycle ring incorporated into the lower stator half and a dialkyl ammonium ion attached to the upper rotor half, forms a [1]pseudorotaxane in less polar solvents such as CH2Cl2. In this self‐complexing system, acid–base‐controlled threading–dethreading movements can be utilized to unlock or lock the molecular motor

  运动的关键：第二代分子旋转电机，其在下定子半部中包含一个DB24C8大环环，并在上转子半部中连接了一个二烷基铵离子，它在极性较小的溶剂（例如CH）中形成了[1]假轮烷2 Cl 2。在这种自复杂系统中，可以利用酸碱控制的穿线-脱线运动来解锁或锁定分子马达（见图）。
• Studies on the Synthesis of Some Xanthonoid Derivatives Possessing Antiplatelet Effects
  作者：Chun-Nan Lin、Song-Chwan Fang、Hsien-Cheng Lin、Feng-Nien Ko、Bor-Jinn Shieh、Hong-Wen Liu、Che-Ming Teng

  DOI：10.1111/j.2042-7158.1994.tb05714.x

  日期：2011.4.12

  2,3- and 3,4-Dihydroxyxanthone react with ethyl 2,3-dibromopropanoate to form the new, substituted 1,4-benzodioxanes 3 and 4, respectively. The regioisomers 3a and 3b; 4a and 4b were separated by column chromatography and characterized for evaluation of the antiplatelet effects in rabbit washed platelets and human platelet-rich plasma. The ethoxycarbonyl derivatives 3a (20 μm) and 3b (20 μm) strongly inhibited the aggregation of rabbit washed platelets induced by arachidonic acid and collagen. The compound 4b showed the most potent inhibition of rabbit washed-platelet aggregation induced by arachidonic acid (IC50 = 8·3 μm). Of the compounds tested in human platelet-rich plasma, compound 4b exhibited the most potent inhibition of primary and secondary aggregation induced by adrenaline (IC50 = 8·6 μm). We conclude that the antiplatelet effects of these four ethoxycarbonyl derivatives are mainly due to an inhibitory effect on thromboxane formation and interference in the adrenaline-receptor interaction.

  2,3-和3,4-二羟基黄酮与乙基2,3-二溴丙酸酯反应，分别形成新的取代的1,4-苯并二氧杂环3和4。通过柱层析分离了3a和3b、4a和4b的同分异构体，并对其进行表征，以评估其在兔洗涤血小板和人血小板富集浆中的抗血小板作用。乙酰氧基衍生物3a（20μm）和3b（20μm）强烈抑制了由花生四烯酸和胶原诱导的兔洗涤血小板聚集。化合物4b对由花生四烯酸诱导的兔洗涤血小板聚集具有最强的抑制作用（IC50 = 8·3μm）。在人血小板富集浆中测试的化合物中，化合物4b表现出对肾上腺素诱导的初级和次级聚集具有最强的抑制作用（IC50 = 8·6μm）。我们得出结论，这四种乙酰氧基衍生物的抗血小板作用主要是由于对血栓素形成的抑制作用和对肾上腺素受体相互作用的干扰。

• Asahina; Tanase, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1941, vol. 61, p. 129,132
  作者：Asahina、Tanase

  DOI：——

  日期：——
• Asahina; Tanase, Proceedings of the Imperial Academy (Tokyo), 1940, vol. 16, p. 297
  作者：Asahina、Tanase

  DOI：——

  日期：——